General, Enantiospecific Synthesis of Cyclopentanoid Monoterpenes (Iridoids). The Total Synthesis of (-)-1-O-Methylsweroside Aglucon

Article abstract of DOI:10.1021/jo00189a047

A total synthesis of optically active cyclopentanoid monoterpenes (iridoids) can be achieved by using (-)-(1S,5R)-cis-3-oxabicyclo<4.3.0>non-7-en-2-one (1) to prepare a key bicyclic synthon, (+)-7.The generality and enantiospecificity of this approach is demonstrated by the preparation of (-)-1-O-methylsweroside aglucon (8).